4-Hydroxy-1,3-(2H)-benzoxathiol-2-one

Base Information

• Chemical Name: 4-Hydroxy-1,3-(2H)-benzoxathiol-2-one
• CAS No.: 95-18-1
• Molecular Formula: C₇H₄O₃S
• Molecular Weight: 168.173
• NSC Number: 71282
• UNII: 37I4BS493F
• DSSTox Substance ID: DTXSID00241714
• Nikkaji Number: J39.067D
• Wikidata: Q27256683
• Mol file: 95-18-1.mol

Synonyms:4-Hydroxy-1,3-(2H)-benzoxathiol-2-one;4-hydroxy-1,3-benzoxathiol-2-one;95-18-1;NSC-71282;1,3-Benzoxathiol-2-one, 4-hydroxy-;UNII-37I4BS493F;37I4BS493F;4-Hydroxy-1,3-benzoxathiol-2-one [INCI];NCIOpen2_000332;WLN: T56 BOVSJ FQ;SCHEMBL1962743;Resorcinol, cyclic thiocarbonate;DTXSID00241714;Resorcinol, cyclic 0,S-carbonate;NSC71282;Thiolcarbonic acid 4-hydroxy-o-phenylene ester;Q27256683;Carbonic acid, cyclic 0,S-ester with 2-mercaptoresorcinol;Carbonic acid, cyclic 0(1),s(2)-3-hydroxy-0-phenylene ester

Chemical Property of 4-Hydroxy-1,3-(2H)-benzoxathiol-2-one

Chemical Property:

• Vapor Pressure: 0.000179mmHg at 25°C
• Boiling Point: 319.6°C at 760 mmHg
• Flash Point: 147.1°C
• PSA: 78.68000
• Density: 1.617g/cm³
• LogP: 1.56010
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 167.98811516
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1)OC(=O)S2)O

Technology Process of 4-Hydroxy-1,3-(2H)-benzoxathiol-2-one

There total 2 articles about 4-Hydroxy-1,3-(2H)-benzoxathiol-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ammonium thiocyanate + recorcinol (108-46-3) → 4-hydroxy-1,3(2H)-benzoxathiol-2-one (95-18-1)

Guidance literature:

With sodium carbonate; copper(II) sulfate; Yield given. Multistep reaction; 1.) water; 2.) water, reflux;

Reference yield:

→ 4-hydroxy-1,3(2H)-benzoxathiol-2-one (95-18-1)

Guidance literature:

nach Monatsh. Chem. 81 <1950> 293;

DOI:10.1248/yakushi1947.84.2_192

Reference yield:

4-hydroxy-1,3(2H)-benzoxathiol-2-one (95-18-1) → 2-thiopyrogallol (2103-60-8)

Guidance literature:

With sodium hydroxide;

upstream raw materials:

recorcinol

Downstream raw materials:

2-thiopyrogallol

Refernces

A combined experimental and computational investigation on the unusual molecular mechanism of the lossen rearrangement reaction activated by carcinogenic halogenated quinones

10.1021/jo5022713

The study investigates the unusual molecular mechanism of the Lossen rearrangement reaction activated by carcinogenic halogenated quinones. It explores how chlorinated benzoquinones (CnBQ) serve as new activating agents for benzohydroxamic acid (BHA), leading to the Lossen rearrangement. The chemicals involved include various chlorinated benzoquinones (such as TCBQ, 2,5-DCBQ, 2,6-DCBQ, 2-CBQ, and TrCBQ), benzohydroxamic acid (BHA), phenyl isocyanate (Ph-NCO), and N,N′-diphenylurea. The study finds that the stability of CnBQ-activated BHA intermediates depends on both the degree and position of Cl-substitution on CnBQs, which can be divided into two subgroups based on their stability. The rate of the CnBQ-activated rearrangement is determined by the relative energy of the anionic CnBQ?BHA intermediates, with the Cl or H ortho to the reaction site at CnBQ being crucial for the stability of these intermediates. A pKa?activation energy correlation is observed, linking the rate of rearrangement to the acidity of the conjugate acid of the anionic leaving group. The study combines experimental and computational methods to provide insights into this novel halogenated quinone-activated Lossen rearrangement, which has implications for understanding the detoxification of carcinogenic quinones and the potential biomedical applications of hydroxamic acids.